DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Election/Restrictions
Applicant's election with traverse of the compound of formula 1 in the reply filed on January 6th, 2026, is acknowledged. The traversal is on the ground(s) that the reference of Geranurimi et al. was published on December 21, 2020, which is after the August 28, 2020, effective filing date of the present application. This is found persuasive. Therefore, the restriction and election requirement on the basis of Geranurimi et al., 2020, Interleukin-1 Receptor Modulation Using b-Substituted a-Amino-g-Lactam Peptides From Solid-Phase Synthesis and Diversification, Frontiers in Chemistry, 8: 610431 has been withdrawn. However, upon further consideration, a new ground for a restriction and election requirement is made in view of Geranurimi et al 2019 (Geranurimi, A., Cheng, C. W. H., Quiniou, C., Zhu, T., Hou, X., Rivera, J. C., St-Cyr, D. J., Beauregard, K., Bernard-Gauthier, V., Chemtob, S., & Lubell, W. D. (2019). Probing Anti-inflammatory Properties Independent of NF-κB Through Conformational Constraint of Peptide-Based Interleukin-1 Receptor Biased Ligands. Frontiers in chemistry, 7, 23).
Geranurimi teaches lactam analogs such as β-hydroxy-α-amino-γ-lactam (Hgl) peptides as interleukin-1 receptor biased ligands [Abstract and Fig 4]. The final product is almost the same as the compound of formula I, with the exception of R3. R3 is taught to possibly be a partially saturated carbocyclic ring (20) [Fig 3]. An artisan of ordinary skill would be able to deprotect (20) using the method to make (12) and use it in place of (12) in the scheme of figure 4 to make a compound reading on formula (I). Therefore, the technical feature that is the compound of formula (I), was not inventive prior to the effective filing date of August 28th, 2020. Thus, the restriction and election requirement withstand under the PCT Rule 64.1
Claims 1-18 are examined. Claims 23 and 25 are withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected method of treating an IL-1 related disease, disorder, or condition, there being no allowable generic or linking claim. Applicant timely traversed the restriction (election) requirement in the reply filed on January 6th, 2026.
Priority
Acknowledgment is made of applicant’s claim for foreign priority under 35 U.S.C. 371. Prior art analysis has been done based on the filing date of the provisional application No. 63/071,492 of August 28th, 2020.
Information Disclosure Statement
The Information Disclosure Statement submitted on May 26th, 2023 is acknowledged and accepted.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
Claims 1-4, 14 and 18 are rejected under 35 U.S.C. 103 as being obvious over Geranurimi et al 2019 (Geranurimi, A., Cheng, C. W. H., Quiniou, C., Zhu, T., Hou, X., Rivera, J. C., St-Cyr, D. J., Beauregard, K., Bernard-Gauthier, V., Chemtob, S., & Lubell, W. D. (2019). Probing Anti-inflammatory Properties Independent of NF-κB Through Conformational Constraint of Peptide-Based Interleukin-1 Receptor Biased Ligands. Frontiers in chemistry, 7, 23; cited in the IDS filed May 26, 2023).
The applied reference has a common inventor with the instant application. Based upon the earlier effective filing date of the reference, it constitutes prior art under 35 U.S.C. 102(a)(1). The reference does not fall under the 102(b)(1)(A) exception as the paper was published more than a year before the effective filing date.
St-Cyr teaches formula (I) and throughout the paper and its supplementary contents [see Figure 4]. The corresponding R1 and R2 are NH2. The final structure does not denote R3 as laid out in claim 1. The scheme shown in figure 4 starts by using β-hydroxy-α-amino-γ-lactam (Hgl) residue (12). However, instead of using the (R,R,R-12) Hgl peptide at that beginning, if the inventors used (R,R,R)-20 Hgl dipeptide see figure 3] and continued with the scheme, the final product would read on claim 1. The method to make (R,R,R)-20 HgI is found in the author’s supplementary content [see S24]. Then, one of ordinary skill could proceed to deBoc (R,R,R)-20 and use it in place of (12). The R3 of the corresponding final product would be a 6-membered partially unsaturated carboxylic ring, reading on claim 1. Thus, it would have been obvious prior to the effective filing date for the inventors to make a compound of formula (I) because Geranurimi teaches all of the parameters of the substituents and how to make formula (I).
Regarding claim 2, R4 and R5 are H as the corresponding R1 taught by Geranurimi et al. is NH2.
Regarding claim 3, the corresponding R2 is NR6R7.
Regarding claim 4, R6 and R7 anticipated by Geranurimi et al. are H.
Regarding claim 14, the stereochemistry of formula (Ia) is the same as the one presented by Gernaurimi et al. [Fig 4].
Regarding claim 18, Geranurimi et al does an experiment treating oxygen-induced retinopathy in rats [section Oxygen-Induced Retinpathy in Sprague Dawley Rats]. In the pharmaceutical composition, the pups received 2 mg/kg/day of peptides 1, 5, or 6 in a phosphate-buffered saline vehicle. Peptide 6 corresponds to the final product taught in Figure 4. The applicant’s elected pharmaceutically acceptable excipient was a saline solution. Therefore, it would have been obvious to an artisan of ordinary skill before the effective filing date to have a pharmaceutical composition comprising of formula (I) and saline with a reasonable expectation of success because Geranurimi teaches that saline is a pharmaceutically acceptable excipient.
Claims 6 and 7 are rejected under 35 U.S.C. 103 as being unpatentable over Geranurimi et al. as applied to claims 1-4 above, and further in view of Mitsos (Mitsos, C. (2006). Isosteres in Medicinal Chemistry. In Baran Lab.)
Gernanurimi teaches a compound similar to formula (I) with the exception of R3 [Figure 4]. The correspond R3 is -OH. Geranurimi does not teach the similarity between a -OH and -NH2 as a substitutent.
Mitsos teaches that bioisosteres are compounds or groups of atoms with the same number of atoms and electrons, producing broadly similar biological effects [slide 1]. The Hydride Displacement Law shows that OH and NH2 are isosteres [slide 1]. Biosteric replacements are ideal for greater selectivity, decreased toxicity, improved pharmacokinetics, increased stability, simplified synthesis and mimicking patented lead compounds [slide 1]. Mitsos goes on the teach that O and NH have similar sizes, both bearing H-bonding donor and acceptor capacities and O and NH have similar Van der Waals radius (1.4 versus 1.5 Å) [slide 3].
Using Mitsos’s teachings, it would have been obvious to the inventor prior to the effective filing date to substitute the -OH of the correspond R3 of formula (I) taught by Geranurimi et al. for -NH2 with a reasonable expectation of success because they are bioisosteres with similar size and electrochemical properties when applied to medicinal chemistry.
Allowable Subject Matter
Claims 5, 8-13, and 15-17 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
The various R3s presented in the listed claims are free of prior art because references searched do not teach why it would be obvious to modify formula (I) of claim 1 to have such substituents. Geranurimi et al, is the closest prior art of record. Geranurimi et al. do not teach or suggest alone or along with any reference of record to to modify R3 in Geranurimi et al. with the claimed substituent group. The structures depicted in claims 15-17 are novel and unobvious.
Conclusion
No claims are allowed. Claims 1-4, 6, 7, 14 and 18 are rejected. Claims 5, 8-13, and 15-17 are objected to
Correspondence
Any inquiry concerning this communication or earlier communications from the examiner should be directed to SACHI JAUHARI whose telephone number is (571)272-3769. The examiner can normally be reached Mon-Fri 9-4.
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/SACHI JAUHARI/ Examiner, Art Unit 1654
/LIANKO G GARYU/ Supervisory Patent Examiner, Art Unit 1654